Diisopropylethylamine → HCID 67439889, compound

HRID 1801281Notes

Reaction equation

HRID 1801281 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O-:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:23]([O-])=O.[CH:26](N(CC)C(C)C)(C)C.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41](Cl)=[O:42]>ClCCl>[CH3:26][O:22][C:20]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:23][C:41](=[O:42])[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=3)[CH:4]=1)[C:17]([CH3:19])([CH3:18])[CH2:16]2)=[O:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 67441230HCID 67441230, compound

Product 1

HCID 67439889HCID 67439889, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To s solution of 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxy late (150 mg, 0.46 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.91 mmol) in dichloro methane (10 mL) was added picolinoyl chloride (77 mg, 0.54 mmol) with ice cooling. Upon completion of addition, the resultant mixture was allowed to stir for 20 h. Solvent was removed in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=3:1) to afford 84 mg of methyl2-(4-fluoro-3-(picolinamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate. Yield: 42.4%.

Workup

  1. additionUpon completion of addition
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6eabae5323544466b458ce3acea99db1
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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